Two Tips for Scaling Sales from 100 to 1,000

Andy Kofoid’s first experience with major sales team growth was at MatrixOne, a Boston-based product management company that was eventually acquired by Dassault Systemes. Over the course of eight years (which included stints as a regional director, head of European sales, and VP of U.S. Sales), Andy went from managing about 20 people to ultimately being in charge of nearly 250 salespeople.

Immediately following his work leading that expansion, Andy signed on with ExactTarget as executive VP of global sales. A few short years later, after ExactTarget was acquired by Salesforce, Andy’s role had evolved to chief operating officer and included responsibilities for customer-facing operations, alliances, customer success, and more. Today, the team he manages is ten times the size of the one he started with.

Guiding a sales organization through substantial growth is a complex job with lots of moving parts, but—having led these two endeavors—Andy believes there are two particularly critical elements that greatly influence the odds of successful expansion.

Leadership: gaining big picture perspective

“I found that growing from fifteen or fifty up to a few hundred people doesn’t require a lot of variation in terms leadership skills,” says Andy. “At that size, I took a lot of pride in knowing most everyone in the organization by name, maintaining personal relationships with each individual, and being very hands-on with all aspects of the business: the deals, the structure, everything from top to bottom.”

But, things change once you break out beyond a few hundred people. “When you quadruple the number of people in your organization, the whole structure falls apart,” Andy explains. “The attributes of a smaller business don’t scale. You can’t know what’s happening with each and every deal or every AE and SDR.”

For Andy, this shift boils down to the idea of accessibility. “In a smaller business—one where you’re hands-on and have personal relationships with each member of your team—you’re very front and center. Everybody knows what you think, so they understand what you’re doing and where you’re going as an organization,” he says. “But, at a certain point the scale of the operation makes it impossible to maintain relationships with each person on the team. Access is limited. How, then, do you effectively convey your vision and direction for operations and process at scale?”

As his accessibility decreased, Andy had to spend more of his time looking at the big picture. “I began focusing more on process, structure, and operations than on having my hands in everything, the way I did with a smaller business,” he says. “This is a big transition point in terms of how a sales leader manages a team—going from operating a high-growth small business to operating a high-growth business at scale.”

Knowledge Transfer: implementing operational rigor

That transition point marked a shift not only in Andy’s personal leadership style and perspective, but also in the day-to-day operations of his extended team. In addition to adjusting internal communication strategy to include a variety of channels and touchpoints (email, Chatter, all-hands calls, and an annual sales meeting), Andy also had to look specifically at knowledge transfer from an operational perspective.

“I learned a lot about effective knowledge transfer at Salesforce because we are a very data-intensive and rigorous business operationally,” Andy says. “Once I understood the cadence, the switch really flipped for me. You don’t have to turn a cold shoulder to people and relationships; but to drive scale and consistency you need to look at the three levers of growth: closing deals ACV, pipeline, and people.”

And with such aggressive growth, the volume of incoming sales hires—the “people” part of the growth equation—can create very real challenges. “One of the biggest questions when you’re bringing headcount into the business is how do you manage their ramp-time and productivity,” Andy says. “In my ExactTarget experience, this was very much an art. In my Salesforce experience, it became much more of a science. We were very good at managing that process by using measurement and iteration to adjust when things weren’t trending in the right direction.”

As the team grew, Andy needed to adopt an entirely different way of training new hires. “We used to rely heavily on in-person training—getting people in a room for a workshop or a presentation,” he recalls. “It’s an effective method, but to do that at scale and keep up with the pace and intensity of our growth is nearly impossible. Managing the influx of knowledge and insight our people need to have via weekly, in-person meetings is not sustainable.”

To paint the picture in more detail, Andy offers this comparison, “If you’re a one-product, 1,000-person organization growing 5-10% a year and not implementing a lot of change, knowledge delivery is very manageable. But, when you’re growing 30% a year and the pace of innovation is increasing your product portfolio exponentially, it quickly becomes overwhelming. Packaging, pricing, the go-to-market strategy—you have to change your whole delivery mechanism for getting up-to-date content to your people.”

Instead of relying on the “analog” training methods that worked when the sales team was smaller, Andy switched gears to take advantage of available digital tools. “We’ve really pivoted to do a lot of knowledge transfer and enablement via the web including go-to meetings and self-learning, which have both been highly effective,” Andy says. “We couple that with in-person meetings every quarter or six months for a deeper dive.”

This approach is working well for Andy and his current team, allowing them to sustain day-to-day productivity and training in a very dynamic sales environment. Looking back over his experiences growing sales organizations to support substantial company growth, Andy offers one last piece of advice: think ahead. “In the early days, most people don’t think about scale enough,” he says. “They don’t think about it in terms of the structure of the business or from a leadership perspective until it’s too late and you’ve already hit the curve. If you apply operational rigor and discipline to how you run the business early on, it will help you scale not only in the initial growth, but also at that inflection point—usually give or take $100 million—where most companies really struggle.”

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